


You Weren't Supposed to Find Out Like This

by 0xenfree



Category: Supernatural
Genre: Alternate Universe - Teenagers, Blow Jobs, Boys In Love, Boys Kissing, Castiel Loves Dean Winchester, Consensual Underage Sex, Crossdressing, Crossdressing Dean Winchester, Dancing, Dresses, Embarrassed Dean Winchester, Established Castiel/Dean Winchester, Fluff, Hand Jobs, Lingerie, M/M, Makeup, Panties, Panties-Wearing Dean Winchester, Smut, Teenagers
Language: English
Status: Completed
Published: 2019-01-12
Updated: 2019-01-12
Packaged: 2019-10-08 14:35:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,343
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17388185
Author URL: https://archiveofourown.org/users/0xenfree/pseuds/0xenfree
Summary: "Castiel watched his footsteps as he walked down the street toward Dean’s house. It had been a few weeks since they had last had time for him to come over, and they both craved time for just the two of them.He quietly walked down the hardwood hallway, hoping that he would be able to catch Dean dancing if he wasn’t heard. The door was cracked open, a small amount of the natural light spilling into the darkened hallway. While he did end up catching him dancing, what he also saw surprised him. Dean was wearing a powder pink, sleeveless dress."Dean finally has the house to himself and forgets that he invited Castiel over for the afternoon. What happens when Cas walks in on him wearing a dress and makeup?





	1. Chapter 1

**Author's Note:**

> Hey guys! First fic of 2019, and I'm excited to post! I'm planning on writing a second part to this and it will probably be up tomorrow, so stay tuned!

 

Castiel watched his footsteps as he walked down the street toward Dean’s house. It had been a few weeks since they had last had time for him to come over, and they both craved time for just the two of them.

The weather had begun to warm up with the emergence of early spring, so Castiel had recently ditched his long winter coat for his thinner, tan trenchcoat. However, even as he walked down the mostly empty streets, he could still feel the chill of the air on his face.

It was a few blocks from his house to Dean’s, but the time passed quickly and he soon found himself standing in front of the light blue, two-story home. Dean had told him yesterday that the door would be unlocked and to just come inside, so that’s what Cas did.

When he passed the threshold of the front door, closing it behind him, he took a moment to warm up before removing his jacket, leaving it on a hook by the door. Once he returned his attention to the rest of the empty house, he could hear the faint music coming from upstairs. He smiled at the thought of his boyfriend dancing to pop music alone in his room, no doubt with a bright smile on his face.

As Castiel climbed the stairs, the sound of the music became louder, and he could make out the tune of “Girlfriend.” _‘Of course he would be dancing to that,’_ Castiel thought, still smiling at thoughts of his lovable dork.

Castiel quietly walked down the hardwood hallway, hoping that he would be able to catch Dean dancing if he wasn’t heard. The door was cracked open, a small amount of the natural light spilling into the darkened hallway. While he did end up catching him dancing, what he also saw surprised him. Dean was wearing a powder pink, sleeveless dress. The loose material swayed around his legs, which Castiel also noticed were shaven smooth, as he shook his hips to the beat of the song.

Castiel silently watched Dean as he jumped around and danced to the song. The sandy-haired boy turned his body in the direction of the doorway. Even from afar, Castiel could see the pink gloss on his lips as he mouthed along to the words, as well as the eyeliner and shiny eyeshadow that decorated his closed eyes. He leaned closer to get a better look at his boyfriend but ended up pushing the door open fully and stumbling into the room. When Dean turned to face Castiel, he could see the half-embarrassed, half-terrified look on his face.

“Um, Cas? Wha-what are you doing here?” Dean stuttered and bit his bottom lip as he spoke. He grabbed his phone and fumbled to turn the music off.

“You, uh, we planned for me to come over? You said the door was open?” Castiel stood awkwardly, trying not to stare but still wanting to take in all of the boy’s look.

“Oh. I did, didn’t I.” Dean nervously rubbed his neck. “I, uh, I didn’t notice that it was that time already… I wouldn’t be dressed like this if I did.” He added the last part quieter than the rest. “I’ll, um, I’ll go change. You probably don’t want to see me like this.” He was watching the floor and Castiel heard him sniffle as he tried to walk past him, one hand reaching up to wipe at his eye.

In a sudden surge of movement, Castiel reached his hand out to grab his arm and stop him from leaving. Dean lifted his head up to look at Castiel in question, his eyes shining with unshed tears.

“Cas? What are you doing?” His expression turned worried when Castiel didn’t let go yet. “You- you don’t want to see me like this. What kind of- what kind of boy wears dresses and makeup?” Dean turned his head away as the tears finally began to fall down his face. “Just let me go change and we can talk about this.” He tried to pull away again, but Castiel tugged him closer and placed his other hand on the small of Dean’s back.

“You don’t have to if you don’t want to,” Castiel said quietly. He didn’t like seeing Dean upset, and he didn’t even really care about the dresses and makeup. He was just a bit shocked at first.

“You- you can’t really mean that.” Dean turned his eyes once again to the floor. Castiel took the opportunity to remove his hand that was on Dean’s arm, and use it to gently tilt his chin up to look at him.

“I do, Dean. I don’t like seeing you cry.” He wiped a tear off of Dean’s cheek before leaning in to kiss the spot where it had been.

“You can’t tell me that you don’t care about the dresses. It’s not normal, and you’re gay so how can you like that I don’t look like a boy?” Castiel swore he could feel his heart break at the sad sound of Dean’s voice.

“Dean,” Castiel leaned in to kiss his boyfriend’s forehead, “I don’t care what you wear, or what you look like. Wearing dresses doesn’t make you any less of a man and if you like it, then I like it on you.” Dean looked at Castiel dubiously. “Okay, sure I was a bit surprised at seeing you in a dress, but now that I’ve had time to process it, the shock has passed. Plus, I think you look kind of, um, cute.” Castiel couldn’t help but avert his eyes when he said that, smiling shyly.

The sound of Dean’s voice caused his eyes to flick back to him. “You really think I look cute?” Castiel could hear the shy excitement in his voice and it made him feel all kinds of warm inside.

“Baby, I think you look beautiful.” Dean smiled brightly at the compliment, even if he was a bit embarrassed by the pet name.

“This wasn’t exactly how I planned for you to find out about the cross-dressing,” Dean confessed, leading Castiel to sit on his bed.

“How long have you been doing it?” Castiel really wanted to know how long he could have been seeing Dean dressed so prettily, not like he wasn’t always pretty, this was just- so different.

“Oh, wow, a few years by now. Charlie found me trying on her clothes once when I was over at her house and decided to just give me some of her old shirts and dresses. I don’t know why we were surprised that they didn’t fit very well, but obviously, they didn’t, so she took me shopping for some clothes of my own. Charlie, along with YouTube tutorials, taught me how to do some simple makeup and yeah. That’s kind of it.”

Dean laughed, remembering some of the things Charlie said to him while shopping. “I can vividly remember my embarrassment when she said, ‘I’ll buy you whatever you want, but you’re buying your own panties.’” Castiel’s eyebrows shot up as Dean said this and the other boy only laughed at his expression.

“Do you,” Castiel started, swallowing thickly, “Do you actually have… Y’know?” Dean flicked his eyes away before awkwardly laughing.

“Heh, um, a few, yeah.” That was not the response Castiel needed, he absolutely did not need to be imagining Dean in women’s panties.

He was pulled back to the present by the feeling of two arms wrapped around his middle. He lifted his arm to accommodate Dean pressing into his side. He pressed his face into the side of Castiel’s chest, and Castiel leaned down to pull Dean’s legs into his lap before moving him completely into his lap.

“Thank you,” Castiel heard Dean’s muffled voice and felt his lips as he spoke against his neck.

“For what, love?” Castiel smiled to himself when he felt Dean smile against his neck at the other pet name.

“For not being too freaked out. For making me feel like this isn’t a big deal. That I can share it with you.” Castiel’s heart swelled at the kind words. He was happy that Dean found him trustworthy.

“You can tell me anything, baby, you know that. I’ll… I’ll love you no matter what.” Dean looked at him with wide eyes when he said that. It was the first time either of them had said they loved the other. “Even if you’re like, a furry or something.” Dean looked skeptical at that.

“Okay, maybe I’d be a little weirded out if you were a furry, but I’m sure I’d get over it. Maybe. Plus, you’re not a furry, so it doesn’t even matter.” Dean raised an eyebrow, smiling. That expression slightly worried Castiel for a moment. “You’re not right? No fursuit hiding in your closet too?”

Dean burst out laughing at Castiel’s worry. “No,” he reassured Castiel, “I’m not a furry nor am I hiding a fursuit.” He smiled at Castiel for a moment longer before leaning up for a kiss. He flipped his legs to straddle Castiel’s lap, continuing to kiss him. They stayed on his bed, kissing and cuddling, for at least an hour.

Castiel lied on his back with Dean’s head resting on his chest. He watched as the fading sunlight played across his face. The shiny lip gloss had long been wiped off, but the eyeshadow covering his eyelids was still vibrant, the sun bouncing off of the shimmery surface.

Castiel was surprised when Dean suddenly interrupted the silence that had settled between them. “You know,” he started, turning his face to look at Castiel, “I could show you those panties someday.” Dean playfully smirked at Castiel, knowing full well that he was flustering the boy.

The brunet tried to keep a stoic face, trying to tease back. “You know what? I think that’s a great idea.”

 


	2. Pink Lace

**Summary for the Chapter:**

> A few weeks after the first chapter, and now maybe Cas will get to see Dean in those panties of his.

**Notes for the Chapter:**

> Aaannndddd... Part 2! I hope you guys enjoy this second part of the story!

 

 

 

It had been a few weeks since Castiel had found out about Dean’s cross-dressing habits, and he couldn’t say that he cared. In fact, since finding out, he only wanted to see more. When Dean told him that he had _panties_ , it was all that Cas could think about.

Every time that he had masturbated within the past weeks, all that Castiel could think of was Dean wearing panties of every color imaginable. Green, blue, pink… All of it, and he was getting tired of only imagining it. He needed to see Dean as soon as he could.

When he got a text from him saying that he had the house alone again, Castiel thanked his lucky stars. He wasn’t sure how he would make it happen, but he would get Dean in those panties.

 

  
Castiel was just about to knock on the Winchesters’ front door when it was opened from the inside. Dean stood there, dressed in a pair of dark jeans and a soft looking, baby blue sweater, with an excited smile on his face.

“Hey babe,” He said, pulling Castiel inside by his hand. Dean pulled him in for a sweet kiss as soon as the door was closed, resting his hands on the back of Castiel’s neck. Cas accepted the kiss and returned the sentiment, wondering why Dean was being so affectionate already, as it usually took a few minutes to get past the awkward state of wondering when the right time to kiss first is. Not that he was complaining though.

When they pulled apart, Dean stepped back and smiled lovingly at Castiel. They stood there for a moment, just looking at each other, before Dean grabbed Cas’s hand again and pulled him to the staircase, and up to his room.

As soon as they end up in Dean’s bedroom, the green-eyed boy is on him again, attacking his mouth with a flurry of kisses. Castiel patiently waits for Dean to get all of his affection out, before speaking. He chuckles before starting, Dean’s arms still holding them close together. “Not that I don’t love it Dean, but what’s with all of the kissing?”

Dean blushes and bites his lip before responding. “I just really love you. That’s all.” Castiel casts his eyes down, a blush of his own heating his cheeks, smiling at his adorable boyfriend. It’s still flustering to hear those words coming from Dean’s mouth.

“Alright,” Castiel responds before pulling Dean in for a kiss of his own, “I love you too.” Dean smiles and pulls out of their embrace.

“So, what should we do? We have the whole house to ourselves.” Oh, Castiel can think of many things he would like to do. Most of them involving him, Dean, Dean’s bed, and lacy panties. Maybe he should wait on those ideas though…

“You choose, I don’t really care.” He says instead. Dean nods before turning to one of the shelves on his wall, lined fully with different records for the player he keeps in his room. Most of them are old ones from his dad, but Castiel knows that Dean keeps a few musical vinyls in there too.

Dean takes his time searching for something to play, perusing through the top shelves first, before bending down to look at the lower ones. As he does this though, the sweater he was wearing rides up a bit and Castiel draws in a sharp breath at what he sees. Over the top of Dean’s jeans, Castiel can clearly see the lacy waistband of a pair of light pink panties.

Immediately, he’s crossing the room and standing behind Dean. He bites his lip before reaching out to caress Dean’s lower back. He hears Dean’s breath hitch when he registers Castiel’s fingers on his exposed skin. Dean looks over his shoulder, making eye contact with Castiel. Cas can clearly see the lust in Dean’s face, his pupils obscuring most of the bright green of his eyes.

“Dean,” Castiel lets out a shaky breath as Dean straightens up and turns around.

“Cas.” Dean’s tongue flicks out to lick at his lips, and Castiel’s eyes follow the motion of it leaving a trail of shine on the boy’s pink lips.

“Are you wearing the panties. The ones that you, um, mentioned last time?” Castiel knows it’s a dumb question because he clearly is, but he can’t think of anything else to say.

Dean nods his head. “Yeah.” He pauses for a moment before speaking again in a hushed tone. “Would you, um, would you like to see?” Castiel can feel his face warming, his body burning with overwhelming need. He nods and sees Dean smile shyly.

Castiel takes a step back to let Dean pass by him, before sitting on the bed. He watches as Dean takes off his sweater and the t-shirt that was underneath it, leaving him in only his jeans. Even his exposed chest alone is enough for Castiel to start getting hard. He unbuttons his pants and lowers the zipper, taking a deep breath before shoving them down his legs and stepping out of them.

Castiel rakes his eyes down Dean’s form. The pink lace rests daintily against his skin, stretching over his hips. He notices how perfectly the underwear cups Dean’s forming erection. How his skin is flushing under Castiel’s scrutinizing eyes.

Cas flicks his eyes back up to Dean’s face before beckoning him closer with a wave of his hand. Dean keeps his bottom lip sucked between his teeth as he slowly approaches Castiel. Once he is close enough, Castiel reaches out both of his hands to rest on Dean’s hips, feeling his warm skin covered by the soft lace. Dean’s breath hitches as Castiel slides his hands around to the back, squeezing Dean’s butt.

Castiel pulls Dean forward, making him land in his lap, straddling him. He runs his hands up Dean’s sides before coming to rest them on his neck and shoulders. “Dean,” He starts, “You look positively exquisite.” He knows that the compliment will make Dean squirm, especially in his increasingly aroused state.

The panty-clad boy surges forward and captures Castiel’s lips in a heated kiss, grinding his hips down against Cas’s. Cas reaches one of his hands down to unbutton his pants and moves the other back down to Dean’s hip to keep him seated on his lap. Dean works his shirt off and then his fingers are tangled in his hair and he’s rocking down into him while simultaneously licking into his mouth, making it hard for Cas to stay focused.

He’s finally able to get his jeans off when he leans back on Dean’s bed, pulling the other boy forward onto his stomach. With the offending item of clothing out of the way, Dean can almost fully feel Castiel’s erection against his ass. He groans into Cas’s mouth as he rocks back against him.

Dean sits up on his knees so Cas can move back on the bed. He makes a surprised noise when he feels Dean’s hand dip into his boxers, pulling out his hard dick. “Dean,” He groans out as the boy starts to stroke him. Dean pulls his hand up to his mouth, licking the palm of his hand to make it slicker. They’ve only done this a few times, but somehow it’s been amazing each time.

Cas can’t hold back the gasps and moans caused by Dean’s ministrations, the sensations quickly becoming all too much. He releases a choked out groan of “Dean!” as he comes. Castiel breaths in deeply, catching his breath after his orgasm, before turning his attention back to his boyfriend. Dean is watching him with rapt attention, eyes wide and cheeks flushed. Castiel swears that he can already feel himself getting hard again when Dean licks his hand clean, sucking on his fingers.

When he finishes with that, Castiel speaks to him, “Dean, come here and lay on your back, baby.” Dean gives him a curt nod before complying with the request. Now Castiel’s turn to service his boyfriend, he places his hand over Dean’s cloth covered erection, slowly rubbing him. He relishes in Dean’s quick breaths and small gasps before removing his hand and replacing it with his mouth.

He licks over the cloth and sucks lightly on Dean’s cock through the thin material. Dean lets out a small, high pitched moan as Castiel works over the head of his cock through the panties. Not wanting to completely ruin them, Castiel works the waistband down, Dean’s dick flopping out and hitting his stomach once released, and tucking it under his balls. He takes a minute to admire Dean. The lovely flush covering most of his body, the heat in his gaze, and his engorged cock.

Quickly, Castiel returns to the task at hand, taking the tip of Dean’s dick into his mouth and sucking on it, which punches a gasp out of Dean. He takes as much of Dean into his mouth as he can, letting his hand stroke the rest of what he can’t fit. Dean squirms as Castiel works his dick in and out of his mouth, tongue circling the head and curling around the shaft.

“Cas,” Dean moans, “Gonna-ugh- Gonna come!” Castiel sucks harder, hollowing his cheeks, and feels Dean’s cum flood his mouth as the boy cries out above him. Sure, Cas has tasted cum before, but feeling it shoot into his mouth as Dean orgasms is a totally new sensation. And Castiel loves it. He swallows the thick liquid in his mouth, smiling at the look that Dean gives him.

Castiel crawls up the bed to lie next to Dean. “So. What’d you think?” Cas asks, curling in close to Dean.

“What’d I think? Cas, that was incredible.” Dean turns his head and smiles dazedly at Castiel before leaning in for a kiss, his tongue flicking into Cas’s mouth. “Hm,” Dean smiles, “You taste like me.” Castiel rolls his eyes at Dean, smiling none the less.  

“So we’re doing that again?” Castiel clarifies. He couldn’t wait to see Dean dressed in more pastel and lace.

Dean presses a kiss to Castiel’s neck. “Definitely.”

 

 

**Notes for the Chapter:**

> Thank you so much for reading this, you guys! Let me know if you want a possible third part to this because I definitely think I have some ideas for one.

**Author's Note:**

> Thanks for reading, and like I said, part two is coming tomorrow!


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